CN108285789A - A kind of hydrogen peroxide fluorescence probe and its preparation method and application - Google Patents
A kind of hydrogen peroxide fluorescence probe and its preparation method and application Download PDFInfo
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- CN108285789A CN108285789A CN201810360906.2A CN201810360906A CN108285789A CN 108285789 A CN108285789 A CN 108285789A CN 201810360906 A CN201810360906 A CN 201810360906A CN 108285789 A CN108285789 A CN 108285789A
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- hydrogen peroxide
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 154
- 239000000523 sample Substances 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 235000019441 ethanol Nutrition 0.000 claims description 22
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 12
- 239000003480 eluent Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 8
- 230000008859 change Effects 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 230000004044 response Effects 0.000 claims description 5
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 4
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 4
- 235000004279 alanine Nutrition 0.000 claims description 4
- 235000003704 aspartic acid Nutrition 0.000 claims description 4
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012472 biological sample Substances 0.000 claims description 4
- -1 bromo naphthalene acid anhydride Chemical class 0.000 claims description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 4
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 3
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 claims description 3
- RWSXRVCMGQZWBV-PHDIDXHHSA-N L-Glutathione Natural products OC(=O)[C@H](N)CCC(=O)N[C@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-PHDIDXHHSA-N 0.000 claims description 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 3
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 claims description 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 3
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229960000310 isoleucine Drugs 0.000 claims description 3
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical compound CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 claims description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 2
- PWKSKIMOESPYIA-UHFFFAOYSA-N 2-acetamido-3-sulfanylpropanoic acid Chemical compound CC(=O)NC(CS)C(O)=O PWKSKIMOESPYIA-UHFFFAOYSA-N 0.000 claims description 2
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 claims description 2
- 150000002171 ethylene diamines Chemical class 0.000 claims description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical class [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical group [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 abstract description 10
- 238000000799 fluorescence microscopy Methods 0.000 abstract description 10
- 229960002163 hydrogen peroxide Drugs 0.000 description 62
- 238000002189 fluorescence spectrum Methods 0.000 description 15
- 239000012452 mother liquor Substances 0.000 description 13
- 238000001514 detection method Methods 0.000 description 11
- 230000005284 excitation Effects 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000012491 analyte Substances 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000005424 photoluminescence Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 1
- 239000004201 L-cysteine Substances 0.000 description 1
- 235000013878 L-cysteine Nutrition 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012490 blank solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007812 electrochemical assay Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000001272 neurogenic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000032696 parturition Effects 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 230000035778 pathophysiological process Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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Abstract
The invention discloses a kind of hydrogen peroxide fluorescence probes and its preparation method and application.The probe molecule formula is C34H38N3O7B has structure as follows：Autofluorescence is green fluorescence to the probe in aqueous solution, and after being responded with hydrogen peroxide, fluorescence intensity reduces at 480nm and fluorescence intensity significantly increases (67.2 times) at 551nm, and can observe by the naked eye the variation before and after fluorescence probe；The probe can also detect the hydrogen peroxide in living cells by confocal fluorescent microscopic, and carry out fluorescence imaging, have certain potential practical value.
Description
Technical field
The present invention relates to a kind of hydrogen peroxide fluorescence probe preparation method and applications, belong to the preparation of hydrogen peroxide probe
Technical field.
Background technology
Hydrogen peroxide is commonly called as hydrogen peroxide, and pure hydrogen peroxide is nattier blue thick liquid, and aqueous solution is water white transparency
Liquid is generally used for surface disinfection.Currently, hydrogen peroxide is mainly derived from metabolism and the drop of organic compound in environment
Solution.Hydrogen peroxide is also human endogenous's property substance, mainly by metabolism when, generate in substance oxidation decomposition course.Research
It was found that hydrogen peroxide is played an important role in the pathophysiological process of biosystem.In vivo, multi-signal is served as to turn
Lead the signal transduction molecule of process.Hydrogen peroxide acts not only as the generation premise of other active oxygens, can also be used as other
The by-product of active oxygen correlated response plays important physiological function.However, when human body endoperoxides hydrogen concentration is raw higher than normal
When reason is horizontal, body injury is will result in, many diseases, including cancer, diabetes, angiocardiopathy, neurogenic disease are caused
And alzheimer disease etc..Therefore, it designs and synthesizes specific good, high sensitivity and there is good biocompatibility
Fluorescence probe, can real-time and accurately the concentration of hydrogen peroxide in organism be detected and is imaged prevention for disease,
Diagnosis, detection, treatment and physiopathologic further investigation all have important directive significance.
Currently, mainly passing through the detection means such as spectrophotometry, electrochemical assay, gas chromatography, liquid chromatography
To detect hydrogen peroxide.These methods apply in general to the hydrogen peroxide in detection aqueous solution and food, are not suitable for biocycle
The detection of the hydrogen peroxide in border, because their detection sensitivity is limited and has destructiveness to biological sample.In recent years, small
Molecule organic fluorescence probe by scientific circles extensive concern, after it has an effect with particular target analytes, fluorescence signal meeting
It changes, to reach testing goal.There is specific selectivity, high sensitivity, response using the fluorescence analysis of fluorescence probe
The features such as the time is fast, and carrying out non-invasive imaging detection to intracellular target molecule can be with real-time online, and image is specifically
Observe signal intensity.So invention can be detected quickly, easily see that look into the hydrogen peroxide fluorescence probe of signal intensity be that have very much must
It wants.
Invention content
The fluorescence probe of hydrogen peroxide can be quickly detected the purpose of the present invention is to provide a kind of, and further provide this
The preparation method and application of probe.
The present invention uses following technical scheme：
A kind of hydrogen peroxide fluorescence probe, molecular formula C34H38N3O7B has structure as follows：
The hydrogen peroxide fluorescence probe, the response time to hydrogen peroxide are 60 minutes or so.
The hydrogen peroxide fluorescence probe, is resistant to O2 -、NO、ClO-, the hydrogen peroxide tert-butyl alcohol, OH-、O2-, half Guangs of L-
Propylhomoserin, l-Glutathione, hydrogen sulfide, Fe3+、NO3-、NO2 -With phenylalanine, alanine, tryptophan, serine, aspartic acid,
The interference of isoleucine and histidine.
A kind of preparation method of above-mentioned hydrogen peroxide fluorescence probe, it includes the following steps：
1) bromo naphthalene acid anhydride 1.0mmol is dissolved in ethyl alcohol, 2.0mmol ethylenediamines is then added, flow back at 80 DEG C anti-
It answers 0.5 hour, after completion of the reaction, the solvent being evaporated under reduced pressure in removing reaction solution by Rotary Evaporators obtains crude product, is used in combination
Silica gel column chromatography column purification obtains neat compounds 1；
2) by 1.0mmol compounds 1 and 1.0mmol lignocaines cumarin acid, 1.5mmol EDCI, 2.5mmol HOBT
It is dissolved in dichloromethane, is then reacted 6 hours or more under room temperature and stirring condition, after completion of the reaction, pass through rotary evaporation
The solvent that instrument vacuum distillation removes in reaction solution obtains crude product, and silica gel column chromatography column purification is used in combination to obtain neat compounds 2；
3) by 0.1mmol compounds 2 and 0.2mmol connection pinacol borate, 0.2mmol potassium acetates, 0.01mmol [1,
1 ,-bis- (diphenylphosphino) ferrocene] palladium chloride is dissolved in Isosorbide-5-Nitrae-dioxane, then in anhydrous and oxygen-free, nitrogen protection
With 90 DEG C under the conditions of be stirred to react 10 hours or more, after completion of the reaction, be evaporated under reduced pressure and removed in reaction solution by Rotary Evaporators
Solvent obtain crude product, be used in combination silica gel column chromatography column purification to obtain target-probe compound.
Eluant, eluent used in column chromatography is dichloromethane and ethyl alcohol volume ratio 50 in the step (1)：1 composition.
Eluant, eluent used in column chromatography is dichloromethane and ethyl alcohol volume ratio 50 in the step (2)：1 composition.
Eluant, eluent used in column chromatography is dichloromethane and ethyl alcohol volume ratio 50 in the step (3)：1 composition.
The synthetic route of probe of the present invention is as follows：
Hydrogen peroxide fluorescence probe prepared by speed of the invention can be used for detecting hydrogen peroxide and biological sample in water environment
The hydrogen peroxide of product.
Above application, specifically, including：
The variation of the fluorescence spectrum of water environment to be measured before and after observation addition hydrogen peroxide fluorescence probe；Fluorescence exciting wavelength is
410nm；
Alternatively, the variation of bioenvironmental fluorescence imaging figure to be measured before and after hydrogen peroxide fluorescence probe is added in observation.
The biotic environment can be living cells.
The variation of the fluorescence spectrum refers to：In fluorescence spectrum, the variation of the photoluminescence peak at 475nm and 548nm；Such as
Peak value becomes smaller at fruit 475nm, and peak value becomes larger at 548nm, then explanation contains hydrogen peroxide.Preferably, using Fluorescence Spectrometer
Observe fluorescence spectrum.
The change in fluorescence refers to：Under the irradiation of 365nm light sources, fluorescence becomes blue-fluorescence from green fluorescence；
The variation of the fluorescence imaging figure refers to：From fluorescence is not observed to observing red fluorescence.Preferably, use is glimmering
Photothermal spectroscopic analyzer observes fluorescence spectrum.
Above application, specifically, including the following steps：
(1) probe compound is dissolved in ethyl alcohol, probe mother liquor is made；
(2) probe mother liquor is added in prepare liquid；
The fluorescence spectrum of prepare liquid, the variation of the photoluminescence peak at 475nm and 548nm are tested with Fluorescence Spectrometer；Such as
Peak value becomes smaller at fruit 475nm, and peak value becomes larger at 548nm, then explanation contains hydrogen peroxide；Wherein, Fluorescence Spectrometer excitation wave
A length of 410nm；
(3) probe mother liquor is added in biological sample, with Laser Scanning Confocal Microscope, uses the light that excitation wavelength is 514nm
Source excitation collects the fluorescence of 460-490nm and 545-575nm ranges respectively；It observes that blue-fluorescence becomes red fluorescence, then says
It is bright to contain hydrogen peroxide.
First, the hydrogen peroxide in aqueous solution can cause the fluorescence spectrum of fluorescence probe to change, and therefore, can pass through sight
The variation degree for examining spectrum in Fluorescence Spectrometer judges content of hydrogen peroxide in solution, to quantitatively detect；Its Monitoring lower-cut
It is 1.4 × 10-6mol/L.Secondly, the living cells for being incubated fluorescence probe II and hydrogen peroxide is carried out by Laser Scanning Confocal Microscope
Fluorescence imaging, the variation of observation blue and green channel fluorescence signal is to reach the hydrogen peroxide in ratio detection biotic environment
Purpose.In addition, using the probe of the present invention, when testing the hydrogen peroxide of aqueous solution using Fluorescence Spectrometer, at 60 minutes or so
The peak value of fluorescence spectrum reaches stable；Have reaction time short advantage, realizes quick detection.
Advantages of the present invention：(1) probe synthesis is simple, and yield is higher；(2) present invention realizes peroxide in aqueous solution
The specificity for changing hydrogen and quickly detection；(3) present invention realizes the detection of hydrogen peroxide in living cells level.
Description of the drawings
Fig. 1 is compound 2 in embodiment 11H NMR spectras.
Fig. 2 is compound 2 in embodiment 113C NMR spectras.
Fig. 3 is 1 middle probe compound of embodiment1H NMR spectras.
Fig. 4 is 1 middle probe compound of embodiment13C NMR spectras.
Fig. 5 is situation of change of the 2 middle probe compound of embodiment with the addition fluorogram of not same amount hydrogen peroxide；Figure
In, concentration of hydrogen peroxide is followed successively by the fluorescence spectrum of 0,5,10,20,30,40,50,70,100,120,150,200 μm of ol/L.
Fig. 6 be probe compound (10 μM) PBS buffer solutions (concentration 25mmol/L, pH 7.4 contains 25% ethyl alcohol) with
5,10,20 equivalents of hydrogen peroxide fluorescence intensity ratio (I in 60 minutes551/I480) variation line graph, excitation wavelength is
410nm。
Fig. 7 be probe compound (10 μM) PBS buffer solutions (concentration 25mmol/L, pH 7.4 contains 25% ethyl alcohol) with
Fluorescence intensity ratio after different analyte responses changes block diagram.Excitation wavelength is 410nm.1, blank；2, O2 -；, 3, NO；4,
ClO-；5, the hydrogen peroxide tert-butyl alcohol；6, OH-；7, O2-；8, L-cysteine；9, l-Glutathione；10, hydrogen sulfide；11, Fe3+；
12, NO3-；13, NO2 -；14, phenylalanine；15, alanine；16, tryptophan；17, serine；18, aspartic acid；19, it is different bright
Propylhomoserin；20, histidine；21, hydrogen peroxide.
Fig. 8 is the fluorescence imaging figure that probe compound (5 μM) is responded with hydrogen peroxide in HeLa cells；In figure, (A1-4)
It is that the fluorescence imaging after 5 μM of probe I I are incubated 30 minutes is added, (B1-4) 30, (C1-4) 75 or (D1-4) 150 μ is then added
Mol/L hydrogen peroxide continues to cultivate fluorescence imaging after sixty minutes；(A1-D1), light field and blue, green channel imaging superposition
Figure；(A2-D2), blue channel is imaged；(A3-D3), green channel；(A4-D4), green is imaged than blue ratio；Excitation wavelength
For 405nm, scale is 25 microns.
Specific implementation mode
With reference to specific embodiment, the present invention is described in further detail.
Embodiment 1
The preparation of probe compound
(1) bromo naphthalene acid anhydride 276mg (1.0mmol) is dissolved in 3mL ethyl alcohol, 120mg (2.0mmol) second is then added
Diamines, back flow reaction 0.5 hour at 80 DEG C, after completion of the reaction, be evaporated under reduced pressure by Rotary Evaporators remove it is molten in reaction solution
Agent obtains crude product, with volume ratio for 50:1 dichloromethane is eluant, eluent with ethyl alcohol, with silica gel (200-300 mesh) chromatographic column into
Row purifying, obtains 290mg yellow solids i.e. compound 1 (yield 80%).
(2) by 319mg compounds 1 (1.0mmol), 261mg lignocaines cumarin sour (1.0mmol), 287mgEDCI
(1.5mmol) and 337mgHOBT (2.5mmol) are dissolved in dichloromethane, and stirring at normal temperature is reacted 6 hours.After completion of the reaction, lead to
It crosses the distillation of rotation evaporation under reduced pressure and solvent (dichloromethane) removing is obtained into crude product.With volume ratio for 50:1 dichloromethane with
Ethyl alcohol is eluant, eluent, is purified with silica gel (200-300 mesh) chromatographic column, and it is (the production of compound 2 to obtain 420mg yellow solids
75%) rate is.1H NMR(400MHz,CDCl3),δ(ppm):1.24-1.27(6H),3.45-3.50(q,J1=6.4Hz, J2=
7.2Hz,4H),3.84-3.88(q,J1=2.8Hz, J2=6.0Hz, 2H), 4.49-4.52 (t, J=5.6Hz, 2H), 6.91
(1H), 7.07 (1H), 7.53-7.55 (1H), 7.82-7.86 (t, J=8.4Hz, 1H), 8.03-8.05 (d, J=8.0Hz,
1H), 8.42-8.44 (d, J=7.6Hz, 1H), 8.57-8.59 (d, J=8.4Hz, 1H), 8.66-8.68 (d, J=7.2Hz,
1H),8.72(s,1H),8.93(s,1H)；13C NMR(100MHz,CDCl3):δ(ppm):24.92,25.60,33.89,
45.08,49.27,96.61,108.42,109.87,110.35,122.20,123.06,128.08,129.18,130.28,
130.68,131.11,131.42,132.23,133.29,148.09,152.48,156.85,157.64,162.56,163.64,
163.77.
(3) 56.2mg compounds 2 (0.1mmol), 50.8mg connection pinacol borates (0.2mmol), 19.6mg acetic acid are taken
Potassium (0.2mmol) and 7.3mg [1,1 '-bis- (diphenylphosphino) ferrocene] palladium chloride (0.01mmol) are placed in round-bottomed flask
In, 3mL Isosorbide-5-Nitraes-dioxane (solvent), which is added, makes reactant be completely dissolved, and is stirred at anhydrous and oxygen-free, nitrogen protection and 90 DEG C
Overnight (10h or more), reaction finishes for reaction.It waits for after completion of the reaction, solvent Isosorbide-5-Nitrae-dioxane is removed by Rotary Evaporators.Most
Afterwards with volume ratio for 50:1 dichloromethane is eluant, eluent with ethyl alcohol, is purified, is obtained with silica gel (200-300 mesh) chromatographic column
34mg yellow solids (yield 56%).Gained yellow solid is target-probe compound.1H NMR(400MHz,CDCl3),δ
(ppm):1.21-1.25(18H),3.42-3.47(q,J1=6.4Hz, J2=6.8Hz, 4H), 3.90-3.91 (2H), 4.57-
4.59 (t, J=4.8Hz, 2H), 6.51 (1H), 6.66-6.68 (d, J=8.0Hz, 2H), 7.41-7.43 (d, J=8.4Hz,
1H), 7.58-7.61 (t, J=7.4Hz, 1H), 7.68-7.70 (d, J=8.8Hz, 1H), 7.76-7.78 (d, J=7.6Hz,
1H), 8.64-8.68 (d, J=7.6Hz, 1H), 8.70 (s, 1H), 8.74-8.76 (d, J=7.6Hz, 1H), 9.01 (s, 1H)；13C NMR(100MHz,CDCl3):δ(ppm):14.79,17.22,39.12,39.27,47.41,57.01,97.32,112.07,
119.31,123.10,125.63,128.33,128.89,131.07,139.88,148.54,150.08,152.76。
Embodiment 2
Probe of the present invention changes from the fluorescence spectrum that different equivalents of hydrogen peroxide react
Probe prepared by Example 1 is dissolved in ethyl alcohol, and a concentration of 1.0mmol/L probes mother liquor (concentration of probe is made
For 1.0mmol/L)；Distilled water is added in the hydrogenperoxide steam generator that mass fraction is 30%, being configured to concentration of hydrogen peroxide is
The hydrogen peroxide mother liquor of 100mmol/L.30 μ L are taken out from probe mother liquor to be added in the centrifuge tube of 3mL, and difference is added and works as
(equivalent refers to the molal quantity of hydrogen peroxide in hydrogen peroxide mother liquor relative to spy to the hydrogen peroxide mother liquor of amount (0-100eq)
The multiple of the molal quantity of needle mother liquor middle probe), with PBS aqueous solutions (the concentration 25mmol/L, pH of 720 μ L ethyl alcohol and different volumes
7.4) it is diluted to 3mL, it is 10 μm of ol/L to be configured to concentration and probe concentration, contains the test solution of 25% ethyl alcohol.It is tested with Fluorescence Spectrometer
Probe changes (excitation wavelength 410nm) from the fluorescence spectrum of different equivalents of hydrogen peroxide reaction solutions, fluorescence spectrum situation of change
As shown in Figure 5.As seen from Figure 5, as gradually increasing for equivalent, fluorescence of the probe I I solution at 480nm is added in hydrogen peroxide
Peak value continuously decreases and the photoluminescence peak at 551nm gradually increases.When fluorescence intensity reaches it is stable when, than probe blank solution
Fluorescence intensity ratio (I551/I485) 67.2 times of enhancing.Experimental result illustrates that probe compound of the present invention can pass through fluorescence spectrum
Instrument detects the hydrogen peroxide in aqueous solution.
Embodiment 3
The change in fluorescence that probe compound of the present invention is changed over time with hydrogen peroxide
30 μ L are taken out from fluorescence probe mother liquor in embodiment 2 to be added in the centrifuge tube of 3mL, and 300 μ L concentration are added
For the hydrogen peroxide mother liquor of 5mmol/L, then 720 μ L ethyl alcohol and the PBS aqueous solutions (concentration 25mmol/L, pH7.4) of 2.25mL it is dilute
It releases to 3mL, it is 10 μm of ol/L, concentration of hydrogen peroxide 0.5mmol/L to be configured to concentration and probe concentration, and the test containing 25% ethyl alcohol is molten
Liquid.With the excitation wavelength of 410nm, its fluorescence spectrum changed over time is tested.As seen from Figure 6, as the time increases, 475nm
The fluorescence intensity at place is gradually reduced and the fluorescence intensity at 548nm becomes larger, and reaches stationary value at 60 minutes or so.
Embodiment 4
Selection Journal of Sex Research of the probe compound of the present invention to disturbance analyte
30 μ L are taken out from fluorescence probe mother liquor in embodiment 2 to be added in the centrifuge tube of 3mL, be separately added into it is following not
With the analyte of concentration：The O of 200 μm of ol/L2 -、NO、ClO-, the hydrogen peroxide tert-butyl alcohol, OH-、O2-, L-cysteine, L- paddy Guangs
Sweet peptide, hydrogen sulfide, Fe3+、NO3-、NO2 -, phenylalanine, alanine, tryptophan, serine, aspartic acid, isoleucine and group
Propylhomoserin.It is diluted to 3mL with the PBS aqueous solutions (concentration 25mmol/L, pH 7.4) of 720 μ L ethyl alcohol and different volumes, is configured to visit
A concentration of 10 μm of ol/L of needle contain the test solution of 25% ethyl alcohol.The fluorescence spectrum variation of detection test fluid after reaction 30 minutes.By
For Fig. 7 it can be found that relative to skip test liquid, the test fluid fluorescence intensity that various chaff interferents are added does not have significant change.However,
Significant changes have occurred in the fluorescence intensity that the test fluid of hydrogen peroxide is added.Experimental result illustrates the probe pair prepared by the present invention
Hydrogen peroxide has good selectivity.
Embodiment 5
The fluorescence imaging of probe compound of the present invention and hydrogen peroxide in cell
10 μ L are taken out from fluorescence probe mother liquor in embodiment 2 is added to the culture dish (PBS containing 1mL for giving birth to HeLa cells
Culture medium) in, concentration and probe concentration is 5 μm of ol/L, is incubated 30 minutes, as control group；In wherein one group of control group sample respectively
The hydrogen peroxide of 30,75,150 μm of ol/L is added, continues to be incubated 60 minutes, as experimental group.It is then burnt micro- with copolymerization respectively
Mirror carries out fluorescence imaging to control group and experimental group, using the light source activation that excitation wavelength is 514nm, collects blue and green is logical
The fluorescence in road, the results are shown in Figure 8.In the fluorescence imaging of control group, it may be observed that strong blue-fluorescence and be barely perceivable
Green fluorescence；However, in experimental group, it is observed that blue-fluorescence gradually weakens and green fluorescence is remarkably reinforced.Experiment knot
Fruit illustrates that probe I I can detect the hydrogen peroxide in cellular environment by Laser Scanning Confocal Microscope, has potential practical application valence
Value.
Claims (8)
1. a kind of hydrogen peroxide fluorescence probe, which is characterized in that its molecular formula is C34H38N3O7B has structure as follows：
2. hydrogen peroxide fluorescence probe according to claim 1, which is characterized in that it is to the response time of hydrogen peroxide
60 minutes.
3. hydrogen peroxide fluorescence probe according to claim 1 or 2, which is characterized in that it is resistant to O2 -、NO、ClO-, peroxide
Change the hydrogen tert-butyl alcohol, OH-、O2-, L-cysteine, l-Glutathione, hydrogen sulfide, Fe3+、NO3-、NO2 -With phenylalanine, alanine,
The interference of tryptophan, serine, aspartic acid, isoleucine and histidine.
4. a kind of preparation method of the hydrogen peroxide fluorescence probe described in claim 3, which is characterized in that it includes following step
Suddenly：
1) bromo naphthalene acid anhydride 1.0mmol is dissolved in ethyl alcohol, then addition 2.0mmol ethylenediamines, back flow reaction 0.5 at 80 DEG C
Hour, after completion of the reaction, the solvent being evaporated under reduced pressure in removing reaction solution by Rotary Evaporators obtains crude product, and layer of silica gel is used in combination
Analysis column purification obtains neat compounds 1；The structural formula of the compound 1 is as follows：
2) 1.0mmol compounds 1 and 1.0mmol lignocaines cumarin acid, 1.5mmol EDCI, 2.5mmol HOBT are dissolved
In dichloromethane, then reacts 6 hours or more under room temperature and stirring condition, after completion of the reaction, subtracted by Rotary Evaporators
It presses the solvent being distilled off in reaction solution to obtain crude product, silica gel column chromatography column purification is used in combination to obtain neat compounds 2；The chemical combination
The structural formula of object 2 is as follows：
3) by 0.1mmol compounds 2 and 0.2mmol connection pinacol borate, 0.2mmol potassium acetates, 0.01mmol [1,1 ,-it is bis-
(diphenylphosphino) ferrocene] palladium chloride is dissolved in Isosorbide-5-Nitrae-dioxane, then in anhydrous and oxygen-free, nitrogen protection and 90 DEG C
Under the conditions of be stirred to react 10 hours or more, after completion of the reaction, pass through Rotary Evaporators vacuum distillation and remove solvent in reaction solution
Crude product is obtained, silica gel column chromatography column purification is used in combination to obtain target-probe compound.
5. the preparation method of hydrogen peroxide fluorescence probe according to claim 4, which is characterized in that in the step (1)
Eluant, eluent used in column chromatography is dichloromethane and ethyl alcohol volume ratio 50：1 composition.
6. the preparation method of hydrogen peroxide fluorescence probe according to claim 4, which is characterized in that in the step (2)
Eluant, eluent used in column chromatography is dichloromethane and ethyl alcohol volume ratio 50：1 composition.
7. the preparation method of hydrogen peroxide fluorescence probe according to claim 4, which is characterized in that in the step (3)
Eluant, eluent used in column chromatography is dichloromethane and ethyl alcohol volume ratio 50：1 composition.
8. a kind of application of the hydrogen peroxide fluorescence probe described in claim 3, which is characterized in that for detecting in water environment
The hydrogen peroxide of hydrogen peroxide and biological sample.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109060739A (en) * | 2018-07-13 | 2018-12-21 | 中国科学院上海微系统与信息技术研究所 | A method of detection hydrogen peroxide |
| CN110016008A (en) * | 2019-04-19 | 2019-07-16 | 南宁师范大学 | The fluorescence probe of specific recognition hydrogen polysulfide and biological thiol |
| CN110172070A (en) * | 2019-06-05 | 2019-08-27 | 商丘师范学院 | A kind of fluorescence probe and its synthetic method and application detecting viscosity and hydrogen peroxide |
| CN110894194A (en) * | 2018-09-13 | 2020-03-20 | 南京大学 | Synthesis of novel fluorescent probe for detecting hydrogen peroxide |
| CN112521413A (en) * | 2020-12-03 | 2021-03-19 | 山西大学 | Two-channel fluorescent probe for detecting viscosity and hydrogen peroxide as well as preparation and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104949946A (en) * | 2015-06-08 | 2015-09-30 | 济南大学 | Application of fluorescent probe to hydrogen peroxide molecule detection |
| CN106632436A (en) * | 2016-10-11 | 2017-05-10 | 济南大学 | Preparation and application of hydrogen peroxide fluorescence probe compound |
-
2018
- 2018-04-20 CN CN201810360906.2A patent/CN108285789A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104949946A (en) * | 2015-06-08 | 2015-09-30 | 济南大学 | Application of fluorescent probe to hydrogen peroxide molecule detection |
| CN106632436A (en) * | 2016-10-11 | 2017-05-10 | 济南大学 | Preparation and application of hydrogen peroxide fluorescence probe compound |
Non-Patent Citations (4)
| Title |
|---|
| LONGWEI HE等: "A new strategy to construct a FRET platform for ratiometric sensing of hydrogen sulfide", 《CHEM. COMMUN.》 * |
| XIANFENG ZHOU 等: "An FRET-based ratiometric chemosensor for in vitro cellular fluorescence analyses of pH", 《BIOMATERIALS》 * |
| XIAO LIANG等: "The dual mechanism ICT-FRET-based fluorescent probe for the selective detection of hydrogen peroxide", 《CHEMISTRY-AN ASIAN JOURNAL》 * |
| 刘瑶: "基于1,8-萘酰亚胺和芘的荧光探针的合成与性能研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109060739A (en) * | 2018-07-13 | 2018-12-21 | 中国科学院上海微系统与信息技术研究所 | A method of detection hydrogen peroxide |
| CN110894194A (en) * | 2018-09-13 | 2020-03-20 | 南京大学 | Synthesis of novel fluorescent probe for detecting hydrogen peroxide |
| CN110016008A (en) * | 2019-04-19 | 2019-07-16 | 南宁师范大学 | The fluorescence probe of specific recognition hydrogen polysulfide and biological thiol |
| CN110016008B (en) * | 2019-04-19 | 2022-04-15 | 南宁师范大学 | Fluorescent probe for specifically recognizing hydrogen polysulfide and biological thiol |
| CN110172070A (en) * | 2019-06-05 | 2019-08-27 | 商丘师范学院 | A kind of fluorescence probe and its synthetic method and application detecting viscosity and hydrogen peroxide |
| CN110172070B (en) * | 2019-06-05 | 2021-11-02 | 商丘师范学院 | Fluorescent probe for detecting viscosity and hydrogen peroxide as well as synthesis method and application thereof |
| CN112521413A (en) * | 2020-12-03 | 2021-03-19 | 山西大学 | Two-channel fluorescent probe for detecting viscosity and hydrogen peroxide as well as preparation and application thereof |
| CN112521413B (en) * | 2020-12-03 | 2021-08-24 | 山西大学 | Two-channel fluorescent probe for detecting viscosity and hydrogen peroxide as well as preparation and application thereof |
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